5of6Vacay is a new resort capsule collection line made in San Francisco. Pictured is the Max dress from the new Maui collection. The pieces are designed to be worn multiple ways.Photo: Bill Reitzel

6of6Vacay's new five-piece Maui collection comes out July 5 and is available at http://vacaystyle.com/.Photo: Bill Reitzel

Packing for vacation these days can strike fear into even a seasoned traveler’s heart. Carry-on restrictions, baggage charges and misrouted luggage are just a few of the hurdles en route to a blissful getaway.

Elizabeth Hynes, a former merchandising and product development executive for Gap and Banana Republic’s outlet stores, experienced the ultimate packing challenge in 2008, when she got married. She and her husband left their jobs, bought a sailboat, and spent 18 months visiting Australia, Bora Bora, Fiji and St. Barts.

“Everyone wants to look fantastic on vacation, but traveling is such a nightmare,” Hynes says.

Even after returning home, she couldn’t shake the idea of re-creating the perfect travel capsule collection. So she left her job last September to start Vacay, which began introducing collections in June. The question, she says, is “Does this piece earn its place in the suitcase?” Each five-piece collection — Antigua, Barbuda, Nantucket, and brand-new Maui and Fiji — when combined with a few wardrobe staples like shorts and white jeans, can create 12 to 16 different outfits.

Her signature $158 Max dress may be the most versatile: Its two pieces — a lined skirt and halter top with shelf bra — can be worn as a maxi dress, top or skirt. Caftan tops do double duty as swimsuit cover-ups, or as tunics.

The clothes are made from travel-friendly rayons, poly chiffons and crinkle cotton gauze, and are produced in San Francisco in runs of 40 items. Hynes, who lives in Marin and has three young sons, sells Vacay online, and at boutique trunk shows, and offers a 20 percent discount to those purchasing five pieces ($450-$600 pre-discount).

As an added bonus, Hynes will throw in a cute patterned tote bag — perfect for fitting just a few multi-tasking garments.

Laura Compton is the Sunday Datebook Editor, overseeing the section’s arts and entertainment coverage. She began her career at The Chronicle in 1998 as a copy editor in the daily Datebook, and since then has worked as an assigning editor, copy editor and writer for the Living, Chronicle magazine and Food sections, and for the past 10 years as Style Editor. Laura introduced coverage of the Bay Area’s independent fashion design and retail scene with features like Window Shopping, #SFStyle and the former SFUnzipped blog on SFGate. A Washington state native, she attended Mills College in Oakland and loves experiencing and finding ways to cover Northern California’s unique arts, culture and lifestyle.